Madeleine's Pits ..... Will Fantasy Become Reality Again?
by Mr. Chain

My friends and I had been at the bar for 2 or 3 hours and were having a good time, or at least that's what I thought. It was a Friday night and though I was tired from the week's worth of working, I took them up on their offer to go out. The bar was sort of tame, which was fine with me, since a night of laying low and having a few drinks with the boys was exactly what I was looking for. But they were getting restless and decided to hit a nightclub just a short distance from where we were.

I originally opted to call it a night, but after they put some pressure on me, I decided to join them. We got to the club at about 1:00 AM and it was packed with the "in crowd", a scene I wasn't in to, at least not tonight. As they headed toward the dance floor, I walked up to the bar to get a drink.

The bar was about three deep with people, so it took me awhile to get up front. But as I did, waiting for the bartender to make his way towards me, I scanned down the bar. My eyes were drawn to a woman seated in the very corner. At first glance, she looked very much out of place. First of all, she seemed much older than the twenty-something women who were all around her. She was also dressed much more traditionally than the rest, wearing a simple, sleeveless black dress. I continued to stare at her, and suddenly realized that she was someone I knew.

The sight of her brought a smile to my face, so when the bartender finally got to me, I ordered a drink for myself and asked him to send one down to her. As he gave me my drink, I started to make my way over to her and arrived by her side just as the bartender placed the drink in front of her. She looked up with a hopeful expression on her face, trying to determine who had sent her the drink. That's when I inched closer and waited for her to turn around. As she did, I smiled back at her.

Though Madeleine seemed delighted to see me in one respect, I couldn't help but notice a hint of disappointment in her pretty brown eyes. But she immediately threw her arms around me and gave me a big hug. As she squeezed and gave me a kiss on the cheek, I could smell the alcohol on her breath. And when she said hello, her speech was slightly slurred, leading me to the obvious conclusion that she had already had too much to drink. But I made nothing of it, setting my arms up on the bar and leaning in next to her as we began our conversation.

I explained how surprised I was to find her in a place like this and asked her what she was doing there. Her face dropped in response to the question and tears started to well in her eyes before she said that she was waiting for someone. I didn't want to ask for more details and she didn't offer any, at least not at first. But as we continued to talk, I could see that her teary eyes were filled with sadness.

Madeleine was a woman in her late 40's or early 50's, I'm not really sure of her exact age. She had come to the gym I had worked in a little over a year ago, looking to get herself back into shape. Her husband had passed away a couple of years earlier and she was finally ready to begin dating again, but before she took that step, she wanted to get into better shape to make herself more appealing. Since I was working as a personal trainer for the gym at the time, she was assigned to me.

Though not excited about the prospect of working a shy, older woman into shape initially, we actually became quite close as time drew on. Eventually, after much hard work and sweat, she got herself into pretty decent shape. Our conversations and my flattery over that period also seemed to help improve her self-esteem, which was somewhat lacking, an accomplishment I was quite proud of myself for doing. Madeleine was so grateful to me for what I had done to not help her not only physically, but also mentally, that she was itching to show her gratitude, a goal she eventually accomplished with flying colors.

You see Madeleine was the woman responsible for making one of my deepest fantasies come true. Not too long before we began working together, I began to admire her armpits, which were deep, sensuous valleys of soft skin. She picked up on my attraction to them and with some prodding, got me to reveal my armpit fetish to her. She obviously had listened intently to my descriptions since, as a gift for my 30th birthday, she organized, together with another woman, an armpit contest, offering me the duty of being the sole judge of the contest. It was a gift I will never forget and helped forge a special place in my heart for her, even though she did not win the contest.

After a few more minutes of conversing, Madeleine grew quiet and shortly thereafter, began to cry. The crying had caught me off guard, seemingly coming out of nowhere. I decided to press her to see what the problem was, and she went onto explain that she had met a guy through an internet dating service and that they had agreed to meet for the first time tonight. He suggested the meeting spot and Madeleine agreed, not knowing anything it was a nightclub. She had felt out of place from the moment she walked in at 10:00 PM, their agreed upon time. Even though it wasn't very crowded then, she knew right away that she would be out of place.

I listened to her go on as I glanced down at my watch and saw that the time was now 1:30 AM, quickly realizing why she was crying, and why she was drunk. Three and a half-hours had passed since the time they were supposed to meet, so it was obvious he wasn't showing.

"I'd really like to get out of here now. I think I've embarrassed myself enough for one night!", Madeleine declared.

She was very upset and I knew that I couldn't leave her alone, so I suggested that she get her coat while I went and said goodbye to my friends. I expected her to say, "Thanks anyway.", but she never did. Instead, she seemed relieved that I had made offer so we agreed to meet in front of the club in 5 minutes, after I had said good night to my friends. I didn't want them to see me leave with her, though I didn't admit that to Madeleine. She was, after all, an attractive woman, but the difference in our ages would have given my friends the opportunity to give me grief about it, and I wasn't going to let that happen!

Greeting her in front of the club, I wasn't sure what she wanted to do, whether she just wanted me to take her home or whether she wanted to go get a cup of coffee, so I suggested the latter. She looked back at me with her pretty, sad eyes, tears still streaming down her face and said that she just to get away from people all together. I stood there and thought for a moment, but before I could come up with a place to go, she surprised me with her suggestion.

"Don't you live around here?", she asked hopefully.

She was right, I lived less than a mile away, though the thought of bringing her back to my place was the furthest thing from my mind. I admit to being mildly attracted to Madeleine, despite our age difference. First of all there were her wonderful armpits! They were so delicious to look at, so soft to the touch that I often had found myself hypnotized by them. And even though she had lost the armpit contest which she had set-up for me, she still had a set of my favorite pits!

I guess in some ways I had a sort of "Mrs. Robinson" attraction to her, though I doubted that Madeleine possessed the sensual qualities of "The Graduate" character. But after debating the suggestion in my head, I finally stuck out my arm suggestively, she hooked her own arm around mine and off we went. The walk took about 15 minutes, a time which she used to describe her situation since last we spoke.

I hadn't seen Madeleine in about 6 months, not since I had quit my job at the gym. I had decided to pursue a career as a physical therapist and in order to do so, gave up personal training. The gig was a full-time day job and I used the nights to study for my license, leaving me no time for the gym. As a result, I could no longer train Madeleine and had lost touch with her. She went on to explain how, after a year of working on her physical appearance as well as her psyche, she had done a great deal of soul searching. So when she was finally ready to start dating again, she knew she was prepared.

She also went on to explain how, much to my surprise, she had only been with one man in her whole life and that man was her husband. She met him while in high school and went on to marry him. So her entire romantic as well as sexual history consisted of being with one man and one man only. She had no regrets about that, but she explained how now, a few years after his death, that she missed being intimate with a man. She shocked me again when she went onto explain that she had never been even remotely experimental in terms of her sex life. She and her husband had always been very traditional and while that had satisfied her at the time, she was now saw an opportunity to explore aspects of her sexuality which she had never had the chance to explore.

I wasn't exactly sure what she meant, but the revelation made me feel a bit uneasy and left me wondering if her remarks were targeted at me. She continued explaining that despite her new way of thinking, she was having a tough time meeting men. When someone mentioned the internet as an option, she decided to join an on-line dating service and before long, met a guy. They exchanged pictures of each other via e-mail and wrote back and forth almost daily for several weeks before finally agreeing to meet.

I was stunned by her revelation, surprised that she had been so bold. After all, Madeleine had always seemed like an "old fashioned" woman to me, not one willing to take such an unorthodox step.

As we finally reached my building and went up to my apartment, the conversation halted until we got inside. I had not expected company, so the place was kind of a mess. But Madeleine took it in stride, and as I took her coat, she took a seat on the sofa. As I sat next to her however, she began to cry once again. I tried to comfort her by putting my arm around her, prompting her to lower her head onto my shoulder. As I stroked her hair, she gradually lifted her head up and stared me straight in the eye.

"He doesn't know what he missed tonight!", she then revealed, "I was ready to let him do anything he wanted to me!"

Again I was stunned by her remarks and began to think that maybe I didn't know her as well as I thought I did. After a few short moments she began to compose herself and stopped crying. I was so amazed by all of the information Madeleine was sharing with me that I hadn't realized what was laying right in front of us on my coffee table. That was when she glanced over at it and noticed them. Sitting right out in the open were a couple of BDSM magazines. I hadn't realized they were there, but sure enough, they were lying right in the middle of my coffee table.

Though I had never tried it myself, I was fascinated by the subject and occasionally picked up a magazine or two to look at the pictures. Madeleine noticed them right away and before I could whisk them away, she picked one up and started to thumb through it. Embarrassed, I said nothing, instead taking a seat next to her and waiting for a reaction.

"Very interesting reading you have here!", Madeleine proclaimed jokingly, her mood now lightening.

I tried to come up with a clever response, but nothing was popping into my head.

"Oh, those are just some magazines a friend left here.", I said nervously.

"A friend eh?", she replied slyly, still leafing through the pictures.

It was not the hard core stuff, that didn't really interest me. The pictures were more of topless women bound and gagged, nothing overly explicit. Madeleine didn't seem offended at all, in fact, judging by the way she was studying the pictures and smiling, I could sense that she was somewhat enjoying herself.

"So, have you ever tried anything like this?", she asked.

I wasn't sure how to respond to the directness of the question. While I had never tried any form of bondage before, I didn't want to sound like a complete loser either.

"No, not really. It's more of a fantasy than a reality to me."

The answer was an honest one and I hoped didn't sound too lame. It must have worked though, as Madeleine seemed to become even more interested as a result of my answer.

"So tell me about your fantasies!", she asked sweetly, her eyes directly staring into mine.

Madeleine had always been very open and honest with me. She had shared a great deal of details from her personal life with me and I had always felt at ease in talking with her. She also had been someone I could share some personal secrets with as well, so I decided to continue to be honest with her.

"Well, I guess I've always fantasized about coming home to find a beautiful, topless woman, bound, gagged and blindfolded. You know, sort of like a surprise with me not having to put any thought into it at all. To tell you the truth, I doubt that I could ever tie someone up myself, so the idea of just having it ready and waiting for me is very arousing."

Madeleine stared back at me sweetly, again, not at all offended. In fact, her eyes displayed a complete fascination at the topic. Gone now were the sadness and tears, replaced by an eagerness to continue the conversation. She continued to browse through the magazine, asking me to pick out my favorite picture. We finally came across a picture of a topless brunette who was tied to a sort of steel cage. She was sweating profusely, her wrists and ankles bound to each corner of the contraption while wearing a blindfold with a ball gag in her mouth. Madeleine paused as if to study every detail of the picture. She then turned and began to ask me a few more questions about my preferences before giving me one which I wasn't prepared for.

"She is really sweating, is that something you like?"

I felt a little embarrassed, but nevertheless explained how the sweat helped to accentuate the contours of the woman's body and was most definitely a part of the attraction.

"I guess it also helps to accentuate her nice pair of armpits too!", Madeleine then giggled.

I laughed back, the two of us sharing an inside joke. She then smiled before placing the magazine back on the table and turning her attention to me.

"I'm sorry to pry, but I'm really fascinated by this subject. In fact, since you've been so good about all of this and honest with me, I'll reveal a fantasy to you as well. You see I'm really interested in this too, but from a different perspective!"

I wasn't sure where she was going with this, but I sat up and listened intently as she went on.

"I guess I've always been sort of submissive in one way or another. First with my husband, I always let him take control in bed and I did whatever he wanted me to do. Don't get me wrong, we never came close to experimenting with anything like this, in fact, our sex life was very tame, but I guess in some way I always hoped that he would be a little more aggressive and ... you know ...take control of me."

She was revealing some pretty personal thoughts, and though still uneasy with her revelations, I couldn't help but listen eagerly.

"To be completely honest, I have fantasized about being tied up. I guess the thought of being dominated by a man and giving up all control is exhilarating to me!", she concluded.

Her voice was filled with passion and I didn't know what to say, again blown away by her. This older, seemingly conservative, very traditional woman was in fact, truly extraordinary. Despite her very conventional lifestyle and appearance, there seemed to be a very sensual, very open-minded woman inside who was dying to get out!

Though thoroughly enjoying the conversation however, I was well aware of the consequences. Madeleine was vulnerable, and though I have to admit that a vulnerable woman is exciting to me, this was not the time to be getting deeper into this conversation. She was probably old enough to be my mother, first of all, and she was drunk on top of that! So weighing all of those factors, I tried to end the conversation and change the subject.

"Well, like I said, this is all just fantasy. In real life, it will probably never happen for me.", I told her.

She looked back at me with a strange, sly grin. Her mind was racing, I could tell, and though she picked up on my inference to change the subject, she wasn't completely done.

"Well you never know. Sometimes fantasy becomes reality.", she purred in her sexiest voice.

I chuckled, trying to ensure that the mood stayed light.

"I guess you're right. After all, who would've thought that I would be judging a real-life armpit contest!", I replied with a chuckle.

Madeleine laughed back before replying, "Yeah, dreams can come true! So I guess that makes me your own, personal genie. Your wish is my command master!"

Though we shared a laugh, the tone of her voice was much more suggestive than I wanted it to be. But we then began to reminisce about the way she had organized the armpit contest, something I had thought would only remain a fantasy for me, though Madeleine had made my wish come true! I began to appreciate her more, but also wondered what was going on in the pretty, little head of hers.

My attempt to change the subject seemed to work though, as Madeleine grew more comfortable and our conversation flowed freely on a different topic. As we continued to discuss my fascination with armpits, she slid closer to me. I didn't back away, though I tried not to move closer either. Though I wasn't interested in sending the wrong signals, I was also becoming aroused just thinking about her lovely pits! In her typical perceptive manner, Madeleine raised her arms to brush her short hair back, in the process revealing those succulent pits for my benefit.

The move was calculated, and I knew it, but at the same time, I didn't mind getting another view of my favorite part of her body. She smiled as my eyes widened while staring into the deep, soft valleys beneath each arm. She then moved in even closer and before I knew it, we were kissing.

Her lips were so soft, her tongue so sweet tasting that I didn't back away. Though I could still taste the alcohol on her breath, it was no longer overwhelming. In fact, she tasted wonderful! We continued to kiss for several minutes before finally we each slowly backed away. Judging by the satisfied expression on her face, I could tell that she had enjoyed it. I had enjoyed it as well, but her next offer was even better. She lifted her arms once again, and without saying a word, summoned me to kiss her pits.

The offer was too tempting to pass up, so as she laid back with her arms raised high, I moved in and began to press my lips into the soft concave beneath her arm. Her skin felt so smooth, like silk as I buried my face in her pit. I licked at her skin, exploring every inch of her armpit with my lips and tongue. It was big enough for my face to disappear into it!

While kissing one of her pits, I began to stroke the other with my fingers, alternating back and forth. Madeleine slouched back deeper into the couch letting her arms fall back and over it as I moved on top of her, my knees now straddling her hips. I continued to adore her pits, kissing slurping, sniffing and caressing them for several minutes as she let out numerous moans, her head falling limply backward. Finally I decided that, while I was in ecstasy, we were getting too hot and heavy, so I backed away before we went further.

Though I was enjoying myself, I also knew that she was very fragile right now and that there was a chance of leaving her even more hurt than when I met her that night. I moved away slowly and gradually so that she was not alarmed and as I sat on her lap, facing her, I could see the gratified expression on her face.

"Thank you for making me feel sexy again.", she whispered, "You've always known just the right things to do and say."

I said nothing, but used the opportunity to slide off of her and take a seat next to her on the sofa.

"So, what's next?", she asked in her sexiest voice, trying to convince me to continue.

"Well, I think I had better take you home.", I offered.

She looked back at me with a disappointed expression and I could see that some of that earlier sadness had returned to her eyes. She then took a deep breath, as if struggling to ask me something, which she finally did.

"Would you mind terribly if I stayed here tonight?", she asked innocently. "I just don't want to be alone tonight."

Her request was so sweet that despite my reservations, I couldn't deny it. I nodded my head in agreement as I got up from the couch. She reached her arm out toward me, asking for help to get up. Grabbing her hand, I gently pulled her from the sofa.

"You can sleep in my bed, I'll sleep out here.", I suggested.

She looked back at me, not accepting the answer.

"I'd rather we both slept in your bed. Don't worry though, we don't have to do anything, I'd really just like to just sleep next you. Is that okay?"

How could I deny her! She seemed so innocent and her request so sincere that reluctantly, I agreed and escorted her into the bedroom. She asked to use the bathroom, so I showed her where it was before handing her one of my tee shirts to change into. I then changed into a pair of shorts and a tee shirt myself before getting into bed and waiting for her to emerge from the bathroom.

A few minutes later the door opened and she stepped forward. With the light still on behind her, she stood in the doorway, reaching her arms over head as she grabbed the frame on either side of the door in her sexiest pose.

"I spent a lot of money on this underwear, so I didn't want to go to bed without showing it to someone.", she purred.

She was wearing a matching black, lace bra and panty set and I was impressed with what I saw. She looked pretty good for her age and I couldn't help but be proud of the part I played in helping her achieve that. Though she didn't have the svelte figure of a twenty-five-year-old woman, she nonetheless could have passed for a plus-sized lingerie model!

Over the past year and a half she had transformed her chubby body into one which looked pretty good. My eyes were immediately drawn to her armpits though, which she was so eloquently exposing for my benefit. But though I had always cherished the opportunity to gaze into her pits, it was hard to prevent myself from looking at the rest of her body.

First of all her chest was quite impressive! It was very large, and though her bra seemed to help lift it, still looked fairly firm. Her stomach was also fairly flat, soft but with some nice curves around her hips. Her legs were also shaped nicely and the lingerie she was wearing offered enough coverage to emphasize her positive features while helping to hide her flaws. A full figured woman, Madeleine had nonetheless done the most with what she had and now seemed proud to show it off. I was proud of her too as I scanned her up and down before finally feeling compelled to react.

"WOW! You really look great!", I remarked, bringing a smile to her lips.

She smiled back at me shyly before purring, "If it's all the same to you, I think I'll just sleep in this.", before walking toward me.

I didn't protest, so she climbed into bed with me, snuggling up alongside me. Though it felt awkward to have her clad only in her underwear, lying in the bed next to me, that didn't stop me from rolling next to her and again beginning to kiss her. We got pretty intense before she rolled onto her back, lifted her arms over her head and clutched onto my headboard. Following her invitation, I prepared to again dive right into her armpits, but she shocked me once more with another offer.

"Would you like to tie me up?", she whispered softly in my ear.

The offer was incredibly tempting, causing me to pause as my erection grew even larger. I gave her offer some serious consideration as she looked up at me hopefully and I could tell that she more than willing. But I knew that she was drunk and that, despite my desires, it wasn't the right thing to do. So in the most complimentary manner, I denied her request.

She was mildly disappointed, but seemed to understand. Not wanting to miss another opportunity to dive into her pits, I nonetheless lowered my face down toward them. With my tongue sticking out, I pressed it against the side of her protruding right breast and began to slowly circle inward toward her right underarm. The tip of my tongue surveyed every inch of her silky pit, my lips bathing it with kisses.

I then did the same on her left armpit, working her into a frenzy as she moaned and writhed below me. But as she was getting more turned on, I knew that I had to stop there and suddenly felt the need to get away for a few minutes before there was no turning back.

I excused myself, much to her dismay, getting up and walking into the bathroom. I didn't need to go, so I just took a seat on the toilet and debated what to do next. I knew that once I went back out and got into bed, there was only one thing to do, and that would forever change our relationship. I began to think the worst, fearing that she might become too attached to me if we were to have sex and ultimately forcing me to hurt her so badly that our friendship would abruptly end.

Though I did want it to go further to be completely honest, I knew that it was not the right time. So finally, after a few more minutes of debate I got up and walked back into the bedroom. Glancing into my bed, I was relieved to find Madeleine fast asleep, her arms still stretched over her head to display her sensuous pits. Not to miss the chance to nuzzle my face in one of them, I climbed back into bed slowly, not wanting to wake her. But then I rolled onto my side and gently lowered the side of my face into the wide-open pit which was right along side me.

It was almost as of her pit was custom made for my face, and as I laid down into it, my cheek felt a sensation it had never experienced before. It was like laying in the softest, down pillow I had ever felt. I then closed my eyes as Madeleine let out a soft moan while still asleep. Eventually I fell asleep myself, my nose wallowing in the delightful smells and my face caressing the most comfortable pillow it had ever slept on!

TO BE CONTINUED?

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